Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

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  • TODOROKI Kenichiro
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • NAKANO Tatsuki
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • WATANABE Hiroki
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • MIN Jun Zhe
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • INOUE Koichi
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • ISHIKAWA Yoshinobu
    Laboratory of Physical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka
  • TOYO’OKA Toshimasa
    Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

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  • Computational Prediction of Diastereomeric Separation Behavior of Fluorescent <i>o</i>-Phthalaldehyde Derivatives of Amino Acids

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We have developed a convenient method for predicting the LC resolution of amino acid diastereomers through computational calculations. For acquiring experimental data, we derivatized 10 amino acids using o-phthalaldehyde and N-acetyl-L-cysteine as fluorogenic diastereomer-forming reagents and analyzed the diastereomers using reversed-phase LC and fluorescence detection. For theoretical chemical calculations, we used the publicly available semi-empirical calculation software MOPAC2012. Using the obtained experimental and theoretical data, we determined the change in analytical resolution with differences in the structure of the diastereomers. From the results obtained, we concluded that greater conformational change through diastereomeric derivatization induced an increase in the contact area with the stationary phase, leading to higher resolution.

収録刊行物

  • Analytical Sciences

    Analytical Sciences 30 (9), 865-870, 2014

    社団法人 日本分析化学会

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